| 24 Oct 23 | r01        | Arnett GardensArnett Garden | 0 - 0 | DunbeholdenDunbeholden |
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| 05 Nov 23 | r03        | Mount Pleasant FAMount Pleasan | 3 - 0 | DunbeholdenDunbeholden |
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| 12 Nov 23 | r04        | DunbeholdenDunbeholden | 0 - 2 | Portmore UnitedPortmore Unit |
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| 26 Nov 23 | r07        | DunbeholdenDunbeholden | 2 - 1 | Molynes UnitedMolynes Unite |
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| 10 Dec 23 | r09        | DunbeholdenDunbeholden | 2 - 2 | Tivoli GardensTivoli Garden |
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| 17 Dec 23 | r10        | Montego Bay UnitedMontego Bay U | 1 - 2 | DunbeholdenDunbeholden |
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| 21 Dec 23 | r02        | DunbeholdenDunbeholden | 1 - 0 | Humble LionsHumble Lions |
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| 27 Dec 23 | r11        | DunbeholdenDunbeholden | 2 - 1 | Waterhouse FCWaterhouse FC |
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| 31 Dec 23 | r12        | CavalierCavalier | 1 - 0 | DunbeholdenDunbeholden |
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| 03 Jan 24 | r13        | Vere UnitedVere United | 1 - 2 | DunbeholdenDunbeholden |
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| 10 Jan 24 | r08        | Harbour ViewHarbour View | 2 - 0 | DunbeholdenDunbeholden |
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| 16 Jan 24 | r14        | DunbeholdenDunbeholden | 0 - 1 | Arnett GardensArnett Garden |
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| 21 Jan 24 | r15        | Humble LionsHumble Lions | 0 - 0 | DunbeholdenDunbeholden |
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| 28 Jan 24 | r16        | DunbeholdenDunbeholden | 1 - 2 | Mount Pleasant FAMount Pleasan |
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| 04 Feb 24 | r17        | Portmore UnitedPortmore Unit | 1 - 1 | DunbeholdenDunbeholden |
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| 25 Feb 24 | r20        | Molynes UnitedMolynes Unite | 2 - 4 | DunbeholdenDunbeholden |
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| 05 Mar 24 | r21        | DunbeholdenDunbeholden | 3 - 0 | Harbour ViewHarbour View |
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| 10 Mar 24 | r22        | Tivoli GardensTivoli Garden | 1 - 1 | DunbeholdenDunbeholden |
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| 20 Mar 24 | r23        | DunbeholdenDunbeholden | 0 - 2 | Montego Bay UnitedMontego Bay U |
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| 24 Mar 24 | r24        | Waterhouse FCWaterhouse FC | 1 - 0 | DunbeholdenDunbeholden |
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| 31 Mar 24 | r25        | DunbeholdenDunbeholden | 2 - 4 | CavalierCavalier |
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| 07 Apr 24 | r26        | DunbeholdenDunbeholden | 4 - 2 | Vere UnitedVere United |